This invention relates to novel ketone pyrazole, thiophene, and pyridine sulfonylurea herbicidal compounds, agriculturally suitable compositions thereof and a method of using them to control the growth of undesired vegetation.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel shortage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
The "sulfonylurea" herbicides are an extremely potent class of herbicides discovered within the last few years. A multitude of structural variations exist within the class of herbicides, but they generally consist of a sulfonylurea bridge. --SO.sub.2 NHCONH--, linking two aromatic or heteroaromatic rings.
EP-A95,925 which was published 12/7/83 discloses herbicidal sulfonylureas of formula ##STR1## wherein Q is, in part ##STR2## R.sub.10 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, CO.sub.2 R.sub.24, SO.sub.2 NR.sub.20 R.sub.21 or SO.sub.2 R.sub.22 ;
R.sub.11 is H, C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, OR.sub.16, CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21 ; provided that when R.sub.10 is other than C.sub.1 -C.sub.3 alkyl, then R.sub.11 is H, Cl, OCH.sub.3, NO.sub.2, or CH.sub.3 ; PA1 R.sub.12 is H or CH.sub.3 ; PA1 R.sub.13 and R.sub.14 are independently H, C.sub.1 -C.sub.3 alkyl, OR.sub.16, F, Cl, Br, NO.sub.2, CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21 ; provided that, when either of R.sub.13 or R.sub.14 is CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21, then the other is H, Cl, CH.sub.3, OCH.sub.3 or NO.sub.2 ; and PA1 R.sub.15 is H or CM.sub.3. PA1 B and C are independently H, halogen, NO.sub.2, C.sub.1 -C.sub.8 alkyl, arylalkyl, C.sub.1 -C.sub.8 alkoxy, haloalkyl, CO.sub.2 R, CONR.sub.1 R.sub.2, S(O).sub.n R.sub.3, SO.sub.2 NR.sub.4 R.sub.5, or optionally substituted phenyl. PA1 n is 1 or 2; PA1 D is 0, S, NH or NC.sub.1 -C.sub.4 alkyl; PA1 R.sub.2 is H, halogen, CF.sub.3, NO.sub.2, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; and PA1 A is 0, S, NR.sub.5 or --C.dbd.N--, PA1 Y is 0, S, or C(R.sub.6).dbd.N; and PA1 R.sub.7 is H, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 haloalkyl, C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 haloalkoxy, C.sub.2 -C.sub.10 alkoxyalkoxy, C.sub.3 -C.sub.5 alkenyloxy, C.sub.3 -C.sub.5 alkynyloxy, phenoxy, benzyloxy, C.sub.1 -C.sub.5 alkylthio or NR.sub.8 R.sub.9. PA1 Y is 0 or S; PA1 Z is 0 or S; PA1 E is N or CH; PA1 R.sub.1 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkoxy, halogen, C.sub.1 -C.sub.4 aIkylthio, NR.sub.6 R.sub.7 or alkoxyalkyl containing not more than 4 carbon atoms; PA1 R.sub.2 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, NO.sub.2, C.sub.1 -C.sub.3 alkoxy, C(W)R.sub.8, SO.sub.2 NR.sub.6 R.sub.7, S(O).sub.n -C.sub.1 -C.sub.3 alkyl or COR.sub.9 ; PA1 R.sub.3 is H, halogen, C.sub.1 -C.sub.3 alkyl, OCH.sub.3 or CF.sub.3 ; PA1 R.sub.5 is H, NO.sub.2, F, Cl, Br, CH.sub.3, CF.sub.3, S(O).sub.n C.sub.1 -C.sub.3 alkyl, COC.sub.1 -C.sub.4 aIkoxy or C.sub.1 -C.sub.3 alkoxy; PA1 R.sub.8 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or alkoxyalkyl containing not more than 4 carbon atoms; and PA1 W is 0 or NOR.sub.10. PA1 B is H or lower alkyl; PA1 D is H, CO.sub.2 R or COAr, halogen, NO.sub.2 or SO.sub.2 NR.sup.1 R.sup.2 ; and PA1 Ar is phenyl optionally substituted with halogen. PA1 R.sub.1 is H or CH.sub.3 ; PA1 R.sub.2 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, nitro, C.sub.1 -C.sub.3 alkoxy. SO.sub.2 NR.sub.c R.sub.d, C.sub.1 -C.sub.3 alkylthio C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, CN, CO.sub.2 R.sub.e, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 haloalkylthio, amino C.sub.1 -C.sub.2 alkylamino di(C.sub.1 -C.sub.3 alkyl)amino or C.sub.1 -C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkylthio, CN, OH or SH; PA1 R.sub.a and R.sub.b are independently C.sub.1 -C.sub.2 alkyl; PA1 R.sub.c is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl, methoxy or ethoxy; PA1 R.sub.d is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; or PA1 R.sub.c and R.sub.d may be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; PA1 R.sub.e is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.1 -C.sub.2 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl; PA1 R' is C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 haloalkyl, C.sub.1 -C.sub.5 alkyl substituted with one or two R.sub.3 groups, C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.5 haloalkenyl, C.sub.3 -C.sub.5 alkenyl substituted with one or two R.sub.3 groups, C.sub.3 -C.sub.5 alkynyl, C.sub.3 -C.sub.5 haloalkynyl, C.sub.3 -C.sub.5 alkynyl substituted with one or two R.sub.3 groups, C.sub.3 -C.sub.5 cycloalkyl, C.sub.3 -C.sub.5 halocycloalkyl, C.sub.3 -C.sub.5 cycloalkyl substituted with one or two R.sub.4 groups, C.sub.4 -C.sub.7 cycloalkylalkyl, C.sub.4 -C.sub.7 halocycloalkylalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl substituted with one or two R.sub.4 groups, phenyl or benzyl; PA1 R.sub.3 is C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, CN, NO.sub.2 OH, OR.sub.5 or di-(C.sub.1 -C.sub.3 alkyl)amino; PA1 R.sub.4 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, CN, NO.sub.2, OH, OR.sub.5 or di-(C.sub.1 -C.sub.3 alkyl)amino; PA1 R.sub.5 is SO.sub.2 CH.sub.3, Si(CH.sub.3).sub.3, C.sub.2 -C.sub.3 alkylcarbonyl or CO.sub.2 C.sub.1 -C.sub.2 alkyl; PA1 E is a single bond or CH.sub.2 ; PA1 W is 0 or S; PA1 n is 0 or 1; PA1 n' is 0 or 1; ##STR17## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino or C.sub.3 -C.sub.5 cycloalkyl; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 aIkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, azido, cyano, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, ##STR18## or N(OCH.sub.3);CH.sub.3 ; m is 2 or 3; PA1 L.sub.1 and L.sub.2 are independently 0 or S; PA1 R.sub.6 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.7 and R.sub.8 are independently C.sub.1 -C.sub.3 alkyl; PA1 Z is CH or N; PA1 Y.sub.1 is 0 or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; PA1 Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 Y.sub.3 is H or CH.sub.3 ; PA1 X.sub.4 is CH.sub.3 ; OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; and PA1 Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; PA1 (a) when X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3,N(CH.sub.3).sub.2 or OCF.sub.2 H; PA1 (b) when X or Y is C.sub.1 haloalkoxy, then Z is CH; PA1 (c) X.sub.4 and Y.sub.4 are not simultaneously Cl; PA1 (d) when W is S, then R.sub.1 is H, A is A-1 and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or 1,3-dioxolan-2-yl; PA1 (e) when the total number of carbons of X and Y is greater than ;our, then the number of carbons of R must be less than or equal to two; PA1 (f) when J is J-1, J-2, J-3 or J-4 then R' is other than C.sub.3 -C.sub.5 cycloalkyl or phenyl; PA1 (g) when J is J-5, J-6 or J-7 wherein E is a single bond, then R' is other than C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.5 alkenyl, phenyl, benzyl, cyclopentyl or C.sub.4 -C.sub.7 cycloalkylalkyl; PA1 (h) when either or both of X and Y are OCF.sub.2 H then J is J-1, J-2, J-3, J-4, J-8, J-9, J-10 or J-11; and PA1 (i) when the total number of carbon atoms of X and Y is greater than four, then the total number of carbon atoms of R.sub.2 and R' must be less than or equal to 7. PA1 J is J.sub.1 to J.sub.10 and E is a single bond; or PA1 J is J.sub.1 to J.sub.4 or J.sub.8 to J.sub.10 and E is CH.sub.2 ; or PA1 J is J.sub.5 to J.sub.7, E is CH.sub.2 and PA1 R' is C.sub.1 -C.sub.5 haloalkyl. C.sub.1 -C.sub.5 alkyl substituted with one or two R.sub.3 groups, C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.5 haloalkenyl, C.sub.3 -C.sub.5 alkenyl substituted with one or two R.sub.3 groups, C.sub.3 -C.sub.5 alkynyl, C.sub.3 -C.sub.5 haloalkynyl, C.sub.3 -C.sub.5 alkynyl substituted with one or two R.sub.3 groups, C.sub.3 -C.sub.5 cycloalkyl, C.sub.3 -C.sub.5 halocycloalkyl, C.sub.3 -C.sub.5 cycloalkyl substituted with one or two R.sub.4 groups, C.sub.4 -C.sub.7 cycloalkylalkyl, C.sub.4 -C.sub.7 halocycloalkylalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl substituted with one or two R.sub.4 groups, phenyl or benzyl; PA1 The scope of compounds within these that are first preferred can be also defined by adding the following proviso to the above described generic scope as proviso (j) when J is J-5, J-6 or J-7 and E is CH.sub.2, then R' is other than C.sub.1 -C.sub.5 alkyl. PA1 R is H, C.sub.1 -C.sub.3 alkyl, phenyl, CH.sub.2 CF.sub.3 or CH.sub.2 CH.dbd.CH.sub.2 ; PA1 X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, Cl, F, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; and PA1 Y is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.2 SCH.sub.3, ##STR19## OCF.sub.2 H, OCF.sub.2 Br, SCF.sub.2 H, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3. PA1 R' is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkyl substituted with 1 to 3 halogen atoms selected from 1 to 3 Cl, 1 to 3 F or 1 Br, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 alkylthioalkyl, C.sub.2 -C.sub.4 cyanoalkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.3 alkenyl substituted with 1 to 3 halogen atoms selected from 1 to 3 Cl, 1 to 3 F or 1 Br, C.sub.3 -C.sub.4 alkynyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.3 -C.sub.5 cycloalkyl substituted with 1 to 3 halogen atoms selected from 1 to 3 Cl 1 to 3 F or 1 Br or cyclopropylmethyl. PA1 A is A-1; PA1 n is 0; PA1 X is CH.sub.3, OCH.sub.3 ; OCH.sub.2 CH.sub.3, Cl or OCF.sub.2 H; and PA1 Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, CH(OCH.sub.3).sub.2 or cyclopropyl. PA1 R.sub.1 is H; PA1 R.sub.2 is H, Cl, Br, OCH.sub.3 or CH.sub.3 ; and PA1 R' is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkyl substituted with 1 to 3 F, C.sub.2 -C.sub.3 alkoxyalkyl, C.sub.2 -C.sub.3 alkylthioalkyl, C.sub.2 -C.sub.3 cyanoalkyl C.sub.2 -C.sub.3 alkenyl, propargyl, C.sub.3 -C.sub.5 cycloalkyl or cyclopropylmethyl. PA1 R' is C.sub.1 -C.sub.3 alkyl. PA1 R' is C.sub.1 -C.sub.3 alkyl substituted with 1 to 3 F, C.sub.2 -C.sub.3 alkoxyalkyl, C.sub.2 -C.sub.3 alkylthioalkyl, C.sub.2 -C.sub.3 cyanoalkyl. C.sub.2 -C.sub.3 alkenyl, propargyl, C.sub.3 -C.sub.5 cycloalkyl or cyclopropylmethyl. PA1 R is H, C.sub.1 -C.sub.3 alkyl, phenyl, CH.sub.2 CF.sub.3 or CH.sub.2 CH.dbd.CH.sub.2 ; PA1 R.sub.2 is H, Cl, Br, OCH.sub.3 or CH.sub.3 ; PA1 R' is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkyl substituted with 1 to 3 F, C.sub.2 -C.sub.3 alkoxyalkyl, C.sub.2 -C.sub.3 alkylthioalkyl, C.sub.2 -C.sub.3 cyanoalkyl, C.sub.2 -C.sub.3 alkenyl, propargyl, C.sub.3 -C.sub.5 cycloalkyl or cyclopropylmethyl. PA1 n is 0; PA1 A is A-1; PA1 X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl or OCF.sub.2 H; and PA1 Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, CH(OCH.sub.3).sub.2 or cyclopropyl. PA1 R' is C.sub.1 -C.sub.5 haloalkyl, C.sub.1 -C.sub.5 alkyl substituted with one or two R.sub.3 groups. C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.5 haloalkenyl, C.sub.3 -C.sub.5 alkenyl substituted with one or two R.sub.3 groups, C.sub.3 -C.sub.5 alkynyl, C.sub.3 -C.sub.5 haloalkynyl, C.sub.3 -C.sub.5 alkynyl substituted with one or two R.sub.3 groups, C.sub.3 -C.sub.5 cycloalkyl, C.sub.3 -C.sub.5 halocycloalkyl, C.sub.3 -C.sub.5 cycloalkyl substituted with one or two R.sub.4 groups, C.sub.4 -C.sub.7 cycloalkylalkyl substituted with one or two R.sub.4 groups, phenyl or benzyl. PA1 J is J-5, J-6 or J-7. PA1 J is J-8. J-9, J-10 or J-11. PA1 J is J-5, J-6 or J-7; PA1 E is CH.sub.2 ; and PA1 R' is C.sub.1 -C.sub.5 alkyl. 26. Compounds of Preferred 25 where when J is J-5, R.sub.1 is H, R.sub.2 is H, E is CH.sub.2, PA1 A is A-1, X is OCH.sub.3, Y is OCH.sub.3 and Z is CH then R' is other then CH.sub.3. PA1 R' is C.sub.2 -C.sub.5 alkyl.
EP-A-87,780 (published 9/7/83) discloses herbicidal sulfonylureas of formula ##STR3## wherein A is H, C.sub.1 -C.sub.8 alkyl or optionally substituted phenyl;
ZA 83/3850 (published 11/28/83) discloses compounds of formula ##STR4## wherein Q is a five-membered, heterocyclic radical which is bound by way of a carbon atom and contains 2 or 3 heteroatoms and which may be optionally substituted by halogen, pseudohalogen, nitro, alkyl, hydroxyl, haloalkyl, alkoxy, alkylthio, haloalkoxy, haloalkylthio, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkylcarbonyl, alkoxycarbonyl, alkoxyalkyl, alkylthiocarbonyl, carbamoyl, alkylaminocarbonyl, dialkylaminocarbonyl alkylsulfinyl, alkylsulfonyl, alkenyloxy or alkynyloxy; and groups such as phenyl, phenoxy or phenylthio, which are unsubstituted or substituted by halogen, nitro cyano alkyl, alkoxy, haloalkyl, alkylcarbonyl, alkoxycarbonyl or haloalkoxy; and also benzyl unsubstituted or substituted by halo%en and/or alkyl.
U.S. Pat. No. 4,127,405 and U.S. Pat. No. 4,169,719 disclose herbicidal thiophenesulfonamides, wherein the thiophene ring may be optionally substituted with CH.sub.3, Cl or Br.
U.S. Pat. No. 4,398,939 discloses herbicidal thiophenesulfonamides , wherein the thiophene ring is substituted with substituent groups selected from C.sub.1 -C.sub.4 alkyl, C.sub.3, alkenyl, OCH.sub.3, NO.sub.2, Cl, Br, SO.sub.2 N(C.sub.1 -C.sub.3 alkyl).sub.2 or SO.sub.2 N(OCH.sub.3)CH.sub.3.
U.S. Pat. No. 4,481,029 discloses herbicidal thiophenesulfonamides, wherein the thiophene ring is substituted with carboxylic acid carboxylic ester and alkylcarbonyl groups or derivatives thereof.
U.S. Pat. No. 4,441,910 discloses herbicidal thiophene sulfonamides, wherein the thiophene ring is substituted with the group represented by R.sub.6 S(O).sub.n wherein R.sub.6 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 aIkenyl, cyclopentyl or cyclopropylmethyl.
European publication No. 13,480(published July 23, 1980) discloses herbicidal pyridine-2-, -3- and -4-sulfonylureas, wherein the pyridine ring may be substituted by Cl, Br, F, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, NO.sub.2 or a carboxylic ester group.
U.S. Pat. No. 4,456,469 (issued June 29, 1984) discloses herbicidal pyridine-3-sulfonylureas substituted by C.sub.1 -C.sub.6 alkyl-, C.sub.3 -C.sub.6 alkenyl-, C.sub.2 -C.sub.4 alkoxyalkyl- and C.sub.5 -C.sub.6 cycloalkylsulfonyl groups.
U.S. Pat. No. 4,518,776 (Swiss priority 7/19/82) discloses, in part, a process for the preparation of compounds of formula ##STR5## wherein ##STR6## R.sub.1 is H, C.sub.1 -C.sub.4 alkyl, halogen, NO.sub.2, CN, NH.sub.2, S(O).sub.n C.sub.1 -C.sub.4 alkyl, SO.sub.2 C.sub.1 -C.sub.4 alkoxy, SO.sub.2 -di-C.sub.1 -C.sub.4 alkylamino, CHO, CONH.sub.2, DC.sub.3 -C.sub.5 alkynyl, CODC.sub.3 -C.sub.5 alkynyl, DC.sub.1 -C.sub.4 alkyl, DC.sub.3 -C.sub.5 alkenyl, COC.sub.1 -C.sub.4 alkyl, CODC.sub.1 -C.sub.4 alkyl or CODC.sub.3 -C.sub.5 alkenyl;
U.S. Pat. No. 4,521,597 discloses, in part, a process for the preparation of compounds of formula ##STR7## wherein ##STR8## R.sub.3 is H, halogen, NO.sub.2, OCH.sub.3 or CF.sub.3 ; R.sub.5 is H, F, Cl, Br, NO.sub.2, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, CF.sub.3, S(O).sub.m C.sub.1 -C.sub.5 alkyl, COR.sub.7 or SO.sub.2 NR.sub.8 R.sub.9 ;
U.S. Pat. No. 4,549,899 discloses herbicidal sulfonylureas of formula ##STR9## wherein X is 0, S, NR.sub.4 or C(R.sub.5).dbd.N;
Japanese Patent Application Number 58-70407 (SHO 59-219,218, laid open 12/10/84) discloses pyrazole-5sulfonylureas of formula ##STR10## wherein A is H, lower alkyl or phenyl;
U.S. Pat. No. 4,370,480 discloses herbicidal sulfonylureas of formula ##STR11## wherein ##STR12## R is H, C.sub.1 -C.sub.2 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl; C.sub.1 -C.sub.4 alkyl substituted with one to four substituents selected from 0-3 F, 0-3 Cl, 0-3 Br, 0-2 OCH.sub.3, 0-1 cyano, 0-1 CO.sub.2 R'.sub.1 where R'.sub.1 is C.sub.1 -C.sub.3 alkyl, CO.sub.2 R'.sub.1, C.sub.2 -C.sub.4 alkenyl substituted with 1-3 Cl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.5 -C.sub.6 cycloalkenyl, C.sub.5 -C.sub.6 cycloalkyl substituted with substituents selected from 1-3 CH.sub.3 or one of CH.sub.3 CH.sub.2, Cl, OCH.sub.3, C.sub.4 -C.sub.7 cycloalkylalkyl. ##STR13## or a single bond; and T is 0 or NOR.sub.1.sup.III.
Japanese Patent Application Number 84-273152 (Sho 86-151188, laid open July 9, 1986) discloses the following compound ##STR14##